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. Author manuscript; available in PMC: 2014 Nov 6.
Published in final edited form as: J Am Chem Soc. 2013 Nov 6;135(44):16720–16735. doi: 10.1021/ja409013m

Table 6.

Michael cyclization and attempted nitrile reduction.

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Entry Conditions Result
1 DIBAL (2.5 equiv.), toluene, −78 °C Recovered SM
2 H2, Raney Ni, B(OH)3, PPTS, IPA, H2O, 23 °C Enamine reduction
3 Cp2Zr(H)Cl, THF, 23 °C Recovered SM
4 1) AlMe3 (2.0 equiv.), then DIBAL (2.5 equiv.) 2) NaBH4, DCM, MeOH, 0 °C 22% yield 75